Poecillastrosides, steroidal saponins from the mediterranean deep-sea sponge poecillastra compressa (bowerbank, 1866)
Calabro, Kevin Kalahroodi, Elaheh Lotfi Rodrigues, Daniel Díaz, Caridad Cruz, Mercedes de la Cautain, Bastien Laville, Rémi Reyes, Fernando Pérez, Thierry Soussi, Bassam
Calabro, Kevin
Kalahroodi, Elaheh Lotfi
Rodrigues, Daniel
Díaz, Caridad
Cruz, Mercedes de la
Cautain, Bastien
Laville, Rémi
Reyes, Fernando
Pérez, Thierry
Soussi, Bassam
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Publication Date
2017-06-26
Type
Article
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Citation
Calabro, Kevin; Kalahroodi, Elaheh Lotfi; Rodrigues, Daniel; Díaz, Caridad; Cruz, Mercedes de la; Cautain, Bastien; Laville, Rémi; Reyes, Fernando; Pérez, Thierry; Soussi, Bassam; Thomas, Olivier P. (2017). Poecillastrosides, steroidal saponins from the mediterranean deep-sea sponge poecillastra compressa (bowerbank, 1866). Marine Drugs 15 (7),
Abstract
The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A-G (1-7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A-D (1-4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2', poecillastrosides E-G (5-7) are characterized by a cyclopropane on the side-chain and a connection at O-3' between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus.
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Publisher
MDPI AG
Publisher DOI
10.3390/md15070199
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Attribution-NonCommercial-NoDerivs 3.0 Ireland